Elder Teachings
by Jauney boy
Summary: Oscar is a bit nervous about taking the next step with his girlfriend, and decides to confine with his bis sister, Ilia, for advice on women. Her lessons are a bit practical but they get the point across, only question now is if Oscar wants to keep getting "taught" by her.
1. First lesson

**Got this ship idea from an old fic I couldn't find anymore, though Oscar was with Cinder instead. Which was the inspiration for one of the chapters in Memorable Festives (check it out). And the plot for the porn is a a bit of a tribute to my old incest centric fics days, but this time it's with siblings rather than parents. **

**Don't know what to expect with such a rare ship and a lesser rare idea for RWBY standards. The incest bit that is, while I've always liked reading incest even before writing for RWBY fanfics. Just hope you're as intrigued as I am. **

* * *

Oscar had just came home and barely nibbled at the snacks his mother made. He wasn't all that hungry as he had some pizza at the Little Caesar's he worked at. He'd been working there for about three months and enjoyed his time, especially over that fact it's where he met his now girlfriend, Nora Valkyrie. They'd been dating for about a month, maybe more, but Nora had told him something that brought about a lot of anxiety and pressure.

He didn't have many friends to ask for help or advice, and figured the knowledge of another woman would help. The only woman he's known closer and longer than any he knew now, someone he could trust. He finished whatever food he could and went upstairs, seeking his sister's room and finding it with the door closed. He approached it and knocked twice, leaning in to hear her permission to come in. When he heard it, he did as she said.

"Oh hey Oscar, work go good tonight?" Her voice gentle for the sake of their sleeping parents.

"It went the same as usual, but there was something after work I need to talk to you about..." He trailed off, looking at the floor and clearly serious over something. They both knew she didn't have any experience in fast food or even retail, so he was obviously asking about something unrelated. Her junior year homework got in the way for jobs.

"Oh? What is it?" She stood up on her bed, looking at him as he sat on the side of her mattress.

"The thing is, Nora said she wanted to go a bit further with me." His blush growing brighter after he remembered her exact words.

"In bed?" Ilia asked.

"Kinda, just foreplay stuff so we can be ready for the real deal when it happens... Still, it's a bid deal, right? I mean she'd been my first for anything, kiss, hand holding, she even jerks me off when her parents aren't home." As soon as that last part slipped, he covered his mouth and his blush was so obvious his whole face almost looked red. Ilia just laughed it off.

"Anyway... I really want to do it, but I don't think I'll do a good job. What If I'm bad it at it?"

"I see." She got up a bit more and sat alongside the same edge as he did.

"Well, yeah it's true girls really like a guy with a good oral skills. It should be expected freshmen like you would start experimenting. And most guys your age can't really do a good job, which is why I had that horrible lesbo phase when I was your age. Oddly enough I never got with a girl though, probably for the best. " She rambled, prompting Oscar to clear his throat and get her attention.

"So what should I do? Any ideas?" He was starting to have doubts, his older sister was his only resort for help here.

"Watch porn I guess? In this day and age there's specific categories for just about anything, especially with what you're looking for. Just don't start beating your dick and forget the lesson." She joked, nudging his side as she laughed. Hoping it'd knock him out of his mopey state. He chuckled but went right back to frowning.

"Right, I tried watching videos on how to cook and I was still bad in the kitchen until mom began teaching me stuff. So without practice, I can't really see my own work, just the work of others." He had a good point there, Ilia realized. After a few seconds of thinking, she decided what she'd been thinking about since he mentioned his problem would've been good to try now.

"Alright, then you can practice with me."

"What?!" He almost jumped off the bed with how much shock he felt, like he was just told he was adopted.

"Why not? It'd be good for both of us. I haven't had any action lately and need to practice for your girlfriend. This is out lucky night, bro. Wanna do it or not?"

"Uhm... S-sure, I guess?" He was still baffled by how clear and casual she was about her proposal.

"Alright, get changed out of your sweaty uniform and come back here. He left as soon as she finished talking, he hadn't even realized he still had his uniform shirt on. The stench probably would've ruined the moment if they tried right away. A few minutes had passed and she heard knocking on her door again, telling him to come back in. Oscar was now clad in his pajamas, but the blush was still the same.

Ilia on the other hand had changed to something fitting without having to try too hard, simply wearing a shirt about three times her size and a pair of black panties. It was too revealing and difficult for Oscar to not get hard, as he did as once he saw her sitting on her bed spread eagle. He also noticed the change of lighting, as she only had her red lamp on her nightstand instead of her bedroom light.

"Okay then, ready for your lesson?" She asked, unable to hide her cocky grin.

"Y-yeah." He said, voice and body language quite timid. Moving closer to her bed as she used her curled finger to make a 'come hither' motion.

"Take off my panties." She said, not knowing the shivers it sent trough his spine. He did so hesitantly, shaky fingers peeling off the fabric past her ankles. As he did, he caught a sight of his older sister's pussy, nothing out of the ordinary from the porn he typically viewed. A piece of beauty with a little triangle of hair right above it.

"Your thoughts?" Ilia asked, not sure why her little brother's opinion on her pussy mattered to her.

"It's... Really pretty." He said, unsure of the right adjective for something he's never seen in real life before. She just giggled before talking back.

"Tell me, what are some important parts when it comes to stimulation?" She figured quizzing him a bit before starting was best. He Looked up at her, giving a confused looked before shrugging and going along.

"Well, there's your pussy lips, the clit, and uh... I got nothing else." He looked embarrassed, but he truly didn't know what other terms there were for the rest. But it was alright, this was a lesson after all.

"You're not too far off, but there's a lot more medical terms for everything. The labia minora and manjora for example, I'll tell which is which later. But the main point is that every little bit deserves as much attention, and there's more than what you can see from the outside. Got it?"

"Sure" He replied.

As much as she would've wanted him to go right away and get her rocks off, it wouldn't be enough for him to learn and use that skill. It's not like his girlfriend and him would hang out and she'd just tell him to get to work right away without anything leading up to that moment. Perhaps they were going a bit too fast.

"Hold on Oscar, before we start I want you to come here. Lay with me." She padded the free space next to her, he just looked over her and decided to go with it. He was lying right next to Ilia and before he knew it, she turned her body to her side and placed her leg around his waist, and one hand gently holding his face lovingly. If anybody walked in there'd be no way to define their position as something else. She held his chin and made him look at her, her smile so sweet and bright.

"There's a bit more to oral than just oral, see Oscar when people are in love and wanna do things special, they have to feel special. There's a matter of foreplay before doing foreplay, understand?"

He nodded, slowly wrapping his arms around her and keeping her close. It felt natural.

"Do you think I'm attractive, Oscar?"

"Of course." He managed to whispered in a breathy voice.

"I want you to say it."

"Ilia, you're one of the prettiest girls I know. You've always been very good looking growing up." He more or less mumbled, wanting to say it but feeling weak when the words came out. Nevertheless, she smiled and caressed his cheek with her hand.

"Thank you Oscar, saying things like that makes me feel special. See?" And with that she closed whatever distance there was between their lips, trying to put in a deep kiss with soft tenderness. But he didn't really reciprocate it, closing his lips like he was getting an embarrassing lip kiss from his grandmother. She pulled back.

"No no Oscar, kiss me just like I was Nora. It's gotta be as real as it can be." He nodded again, before leaning in this time and meeting his sister's lips once more. This time their mouths were open and they began to make out like they've done with previous partners before. Eventually a rhythm was founded as lips softly pressed against one another as they kiss, before bringing in some tongue. Ilia's went in his mouth first, finding his and wrestling their muscles together in a heated frenzy. When they had to break for air, Ilia gave another command.

"I want you to kiss my neck." She said, he complied without a missing a beat. He pressed his mouth to her neck and began to suck, occasionally licking it and getting it slick.

"Mmm yeah, that's it Oscar~ Right there." She moaned carelessly, bringing a hand to the back of his head to guide him to her best spots. She had craned her neck to give him more access, had he been on top, she would have wrapped her arms around his neck.

"Help with my shirt." She said, hoping he'd get the clue. Her voice was so full of heated lust and breathy she didn't expect it to sound the way she did. Regardless, Oscar did as he was told and pulled back to give her space. She lifted her shoulders from the bed and arched her back, before he removed her large shirt and threw it elsewhere. Her breasts were now exposed, he went back to kissing her while his hands roamed over her chest. He didn't need to be taught how to deal with a woman's breast, second base is as far as he went with Nora.

Her moans into the kiss were a good sign his hands were doing a good job, so there was no issue in his mind that Oscar should get right to using his mouth. He kissed down her neck and was going straight to the nipple, until Ilia stopped him with her hand.

"I know you're about to suck my nipple, and you will, but... Don't assume it to be the only place of pleasure. I felt good when you squeezed most of my boobs, so use your mouth around too." She said, not exactly honest but still wanted this to sound like something educational. Truth is she doesn't care if only her nipples were sucked. Oscar just nodded in return and began kissing around her petite breasts, seeming much bigger than he thought. But the shirt helped hide the true size. He kissed and licked around the under-boob, sides, and cleavage before getting to her nipple. All the build up had gotten her more anticipated and pleased when he finally did.

"Yes, Oscar... That's it, ah~" She ran her hands through his hair before gripping a handful, careful not to tug on it.

"Mmm, u-use your tongue, a bit rougher." She cooed, careless about her volume as she moaned freely, her hand holding his head close to suck her nipples. Oscar did all she said without question or pause, tiny shock waves of pleasure coursing through her, he almost enjoying it as much as she did. That almost being that Ila felt her thighs dripping and her pussy was soaked, and as much as she wanted to play with herself, she still had to teach Oscar the basics.

"Touch me Oscar." She moaned without thought, her mind must've figure if she couldn't do it, she'd tell Oscar too. But before she could add something else to make it sound teaching, Oscar's hand quickly found itself between her thighs.

"_Fuck_~!" She whisper-screamed, labored breathing making it hard to speak but still loud in her room. She expected him to shush her and give her an angry look, but all her little brother did was lean back in and seal her lips with his. Their kiss was as deep and passionate as before, but much quicker.

"You're so wet Ilia." He remarked, his hand rubbing along her moist folds.

"K-keep doing that, use your thumb on my clit. You remember where it is?" Another nod.

"Oh fuck, Oscar... Be a bit, faster and harder... and... Just like that, little circles." Her face slowly contorted with every minute, her body feeling more electric and heated with his hands bringing her close to orgasm.

"Don't stop, almost done." She said fast, her body writhing in place and her moans drawing on longer than the last. It took a good 17 seconds until Ilia was unable to hold back her cry of pleasure as she came. Her thighs squeezed around his hand and her arms held him close, both their heavy breathing bouncing off one another and letting them know how real and genuine this was.

"Oscar... That was amazing." She sighed, using all the strength she had to lightly caress his face.

"I just... I actually made you cum." He said in realization on what just happened. He made out with his older sister, played with her boobs, and just made her cum with his hands.

"Damn right you did, and I loved it." She then pulled him in for a kiss, this one being more chaste as they just laid to embrace one another, enjoying the feeling of being so close. They gently kissed each other until Ilia pulled back.

"Now you're going for the real deal." She said, spreading her legs again and giving the hint. He caught on, smiling at her before kissing his way down his older sister's body and taking his time at it as well. As anxious as Oscar was, his eager desire to taste her pussy outweighed his nerves. Once there, he pushed his mouth to her lips and stuck out his tongue as if he were french kissing her again, though his tongue was a lot faster and struck out deeper. The taste was much more than he imagined, sweet like her soul and a bit salty from her sweat.

"Alright Oscar, put your mouth around my clit and suck. Just like that... Swirl your tongue at the same time, i-if you can... Mmm~" Her moans rang out again, encouraging Oscar and giving him audible direction on how to please his sister just like he had before. Ilia found herself grabbing her breasts and squeezing them, before one of her hands grabbed the back of his head without even thinking about it.

"Yes yes yes, almost there bro. Don't stop, please~" She groaned, her eyes rolling back to her head and her back arching. Nearly a minute of Oscar's tongue exploring his sister and said girl gasping and bucking her hips along his face. Finally, she collapsed before releasing herself over his face and going weak, panting heaver than before.

Oscar smiled at his work, licking away whatever sweet juices remained in her inner thighs, every stroke of his tongue made her sensitive body shiver. He was about to lick the few drops before Ilia's hand grabbed his and brought it to her mouth, before placing his fingers in her mouth and sucking them clean of her cum. She smiled around his fingers and gave a small moan upon tasting herself.

"You uh, like the taste too?" He asked, a bit surprised to see his sister eat her cum just as he did. She pulled back to answer.

"Well yeah, don't you?" She asked, grinning.

"Of course, just kinda surprised." He shrugged.

"Well I like it. So baby brother, I think we covered every important part of your training. I'd give you an A for a final grade, you were better than some guys I've had before I must admit."

"Great, that's a load of my shoulders... Thanks, Ilia." He said before kissing her cheek and making way to get off the bed, until she grabbed his shoulder. As he moved, Ilia could make out the bulge in his pajama shorts, reminding her that foreplay was a two-way street. And she loved to please as much as she loved being pleased. And with the latter already being taken care of...

"Wait, Oscar?" He turned to her.

"Yeah?"

"I just thought, it might be best for you to know what doing a good job does for you... I can't let you go without giving you something in return." His eyes went wide in excitement as he heard his sister say that.

"Really? You would?" He said, getting back in his place on the bed.

"Well you made me feel good, I wanna pay you back, okay?" She said, looking him in his eyes.

"Wow... So where do I go?" He still asked, not sure what she had planned. Ilia just giggled before patting his spot next to her.

"Right here, and pull off your bottoms~" She purred, moving to the foot of the bed. Greg sat where she told him, his back against the wall and sitting comfortably. What happened next was yet another surprise. The sight of his older and almost naked sister crawling up from the edge and resting her arms on his lap as she examined his cock made him throb. Which of course, she saw happen.

Ilia took Oscar's erection in her hand, looking it up and down. Pretty big even at his age, maybe 6 inches at most. Any girl in the future would be lucky to have it, a part of Ilia's mind made her think she was one of them even after this supposed one time thing. Only thing she didn't like was his obvious lack of landscaping, a bit too much hair at the base as well as his sack. And what a shame, she wanted to suck his balls at some point.

She quickly licked her lips before bringing her mouth to his tip, once she did, she lowered her head and quickly deep throated him.

"Oh fuck." He grunted, leaning forward a bit as she took him in. Ilia's head bobbed at a rapid pace and her hand held firm at the base to increase pleasure. If her occasional deepthroat didn't already. Having not had a girl even touch him before made Oscar feel things he's never felt before. Foreign feelings and her moderate expertise brought him to a finish much faster than his hands ever did.

"Gonna cum gonna ngh!" He groaned, feeling his legs tremble due to his impending orgasm. As this went on, Ilia quickly thought about his finish. It would probably be a big load, and she loved those. The more to swallow the better, and it would be a nice substitute from being able to play with his balls. She brought her tongue to swirl around his tip as her mouth suckled on it. This brought more than enough electric pleasure to course through the underaged boy's body before he released. Iila kept her mouth seals on his cock as he fire spurts after spurts of his warm essence right into her mouth. Anything at all she could feel was gleefully swallowed with a moan of satisfaction.

As soon as Oscar was done cumming into his sister's mouth, his head fell back to rest on the wall, he felt like a mech that had been shut down and couldn't move. All he felt and heard was the sound of Ilia's mouth releasing his cock with a lout _'pop'_

"Did you like that?" She asked, most likely sarcastically as she could see how clearly stunned her little brother was after sucking him off. He wanted to say it was the most magical thing ever and that he loved his sister for it, but he remembered. Nora, the whole reason they were doing what they were doing. This wasn't supposed to be about his sister confessing anything, as much as he found himself not liking that fact for whatever reason.

"I wanna say it's the best I've ever had, but we know it was the only one I've had." He joked. Ilia laughed along with him.

"Alright little bro, I think we're done here. And for the sake of yourself and the rest of the world, shave yourself a bit." She advised. Oscar just blushed again.

"I-I'll get on that." He said before leaving her room.

And with that, the two siblings went to bed for the night and couldn't be more at ease with how things turned out. Their only distraction was the nagging feeling of wanting to do it again.


	2. Advanced

The next day went just like the last, work and school. Ilia back home before her brother while her parents were already getting ready for bed by ten, while she got things prepared for their next session. She wore a black thong saved mainly for special guys, a much smaller shirt that exposed her midriff, and lit a few spare candles around her room to surround the bed. She texted Oscar earlier in the day to come to her room after his nightly shower, which happened as soon as she heard knocking on her door.

"Come in!" She answered, as if he needed permission.

"H-hey." Oscar sheepishly greeting his sister, feeling nervous as he saw the beautiful sight of his revealing sister laying back spread eagle. She just smirked at him and made a 'come hither' motion with her pointer finger, he slowly approached her before closing the door. Though her smirk faltered as she saw his attire, typical pajama shirt and pants. A far cry from her outfit for the night.

"You should be naked right now." She more commanded than suggested, but Oscar still stood without doing anything.

"Uh, what?" He asked, perplexed.

"Did you really think one night of experience was gonna cut it? You don't go to the gym once and think you've already got what you were working for, it takes more and more practice." As truthful as her words were, Oscar couldn't help but notice some ulterior intention behind her words. Regardless, he couldn't really disagree with her.

"Right..." He mumbled before slowly shedding off his clothes. And much to her desire, Ilia noticed every trace of hair above his dick was more or less gone. He didn't just trim, he got rid of any proof of hair. She smirked, before taking off the rest of her clothes before him. She could already see his adolescent cock twitching as he stared at her naked body.

"So, how do we start this time?" He asked, wondering if they would try anything new.

"It's just going to be the same like last night, except I won't tell you what to do this time. I hope you paid attention."

"Okay, I can manage." He said mostly to himself to gain confidence for the task.

He then got into bed with his sister and pulled her close once she was in his reach, placing a deep kiss on her lips. Without being told what to do now, he was able to take his time and do what he liked, going slow and intimate just like he did with Nora. He brushed her hair behind her ear before pulling back and looking into her eyes.

"You are so unbelievably beautiful, Ilia. Not just your body, but who you are as well. Being able to teach me how to be better in bed without asking for anything else is one of the kindest things you've done for me." He said, this time the compliment felt more real, personal. Not having to tell him to say it this time made it special.

"Thanks Oscar, you're so sweet." She said before caressing his cheek and pulling him in for another chaste kiss. But when something Oscar remembered to ask earlier finally came back, he pulled away.

"By the way, I've got a question."

"Shoot."

"Am I going to be going down on Nora first? Or does the order matter?" Something he wondered since last night, unsure if eating out was meant to be first or last. Ilia just giggled again, as much of a loving spirit her brother was, he was adorably naive.

"Yes, it does matter. See, girls can cum a lot in one session, while guys just cum once and they're typically done and some might not care enough to get their girlfriend off... I would know. So to play it safe, it's best if you make a girl cum first before you do. And trust me, the patience is worth it. You wanna feel good? Make her feel good first." She said, hoping her answer was satisfactory. Oscar just nodded and they went back to making out. Oscar had done some homework and tried out somethings he learned about.

He kissed up and down all sides of her neck, peppering her face with tiny kisses and tried some dirty talk to whisper right beside her ear. His lines weren't that bad, but the fact they came from her little brother took out some of the initial impact. Regardless, Ilia was feeling heated and electric as much as last night, if not even more. Her mind wasn't too distracted with teaching or coaching him on what to do with her body, as he was now in full practice on how to treat her.

And when he went down on her? It was out of this world. She didn't have to say anything and he was instantly better than before, his tongue touched every right part the right moment. And when he curled his finger once it was inside her, Ilia had came so hard she actually squirted, his face being the fortunate target. To which he happily licked up with greed.

Ilia laid in her bed, a shivering and writhing mess of orgasmic bliss. There was no way her brother should've been better than some of her older boyfriends, but the proof was there, she could feel it. She could feel her wet pussy getting licked clean and her chest heaving from her panting. It had been too long since she's had such an explosive orgasm.

"Fuuck, that was amazing Oscar~" She moaned as soon as his face left her legs. He smirked and got up before placing a gentle kiss on her pussy, making her jolt a bit due to the sensitivity.

"I could tell~" He replied, hands still on her thighs. He then went over to her side and pulled her in for another cuddle. She hugged him back with weak strength, not that he could blame her.

"By the way, when are you and Nora going to do this?"

"Saturday, took a bit of convincing the manager but she managed to get us the same day off. So we might go on a date and then go to her place, she only lives with an old friend. I thought he was her boyfriend but she says he's like a brother since they've know each other so long. Either way I've already met him and he's nice enough to know boundaries."

"I see, so only a few more days for practice... Guess we'll have to keep at it until then~" She said with a grin, kissing his cheek before crawling down his body. She grabbed his cock which must've been hard since they started, and to be that aroused for that long wouldn't do, especially with how good he made her feel. Soon enough Ilia had her brother's cock in her mouth and was blowing him with every skill she knew, and enthusiasm to add onto it. And much to her surprise, Oscar lasted a decent amount of time. 5 minutes at the very most before her mouth was getting filled with cum, which she drank down and continued to suck him off a bit even after he came.

"Fuck, I'm surprised you drank it." He said, finding just the pure knowledge that she drank his cum was a turn on.

"Well you drink mine, right?"

"Yeah, just didn't think some girls actually did outside of porn."

"Some do, some don't. But I do. Now, we should get to bed. I've got a good plan for us tomorrow." She said before pulling the blanket over herself while Oscar dressed and walked out. Wondering whatever it was she had planned.

* * *

The next followed just the same. Work, shower, then changing. Oscar opted to just wear boxers this time, no need to waste time before getting whatever this special plan was. The whole day he'd been thinking about this, even finding himself having to ask Nora to repeat herself when they were talking in class and lunch, his mind too focused on whatever heavenly pleasures awaited him. And now, the night was here.

But before he could get to his room to spray on some body spray for the occasion, he opened his door to find Ilia already waiting for him on his bed, only wearing a very tight t-back thong. She looked at him with a sultry gaze, noticing his rapidly growing tent from his boxers. Like before, she used her finger to make a 'come hither' motion to make him approach. He did, but she held out a hand once he was be the edge of the bed. He stopped, before seeing her slowly crawl across the bed to meet his bulge face to face. She was at perfect level with him as she brought her fingers into the hem of his underwear, before pulling down and revealing his erect cock.

She licked her smiling lips before grabbing the base and getting to work. She was slow at first, wanting to get him lathered up before taking him deep. She used her tongue in more ways since the last time, thanks to him shaving Ilia had no reluctance to lick every inch of his cock. What really made him groan was the unexpected switch from his cock to his sack, feeling Ilia nuzzle into his balls before sucking one into her mouth. She'd suck one before alternating to the other, all while stroking his length.

The two siblings went on for a few minutes until Ilia felt too worked up to just serve him now. She had her other hand playing with herself inside her panties, but her fingers wouldn't suffice anymore. She pulled back, gave a kiss to his tip, and spoke.

"Get on the bed." She said, seeing him follow her command quickly as he kicked his boxers away and was lying down, looking at her. She stood up on her knees and carefully brought herself over his face, her wet pussy inches from his mouth as she could feel his hot breath grazing her sensitive folds. She shivered before talking once more.

"Now Oscar, eat my pussy while I suck your dick. Show me how good you are at giving while you also receive~" Ilia wasn't sure if this lesson was vital for his training, as she was fairly certain some experiencing high schoolers wouldn't go as far as to sixty-nine so early. Regardless, the more wisdom he had the better, right? At least that was Ilia's point of view, and Oscar was so enamoured by the physical pleasure he couldn't care enough to question her methods.

Before Ilia could craft a good reason for this, she felt his tongue prod at her pussy. His hands then went up to grab her ass, spreading it for easier access to his target. Ilia was already moaning before she could suck him again, and she wasn't one to be turned into a moaning mess by her little brother. Acting fast, she leaned down and quickly devoured his whole prick, every inch in her mouth and down her throat. It was so unexpected Oscar almost felt like cumming right then and there, but held strong as Ilia proceed to choke and gag herself on his prick. All while his tongue was in Ilia's pussy as far as he could stick it.

They continued to sixty-nine to their own heart's content, very focused on the pleasure instead of the lesson, not that they even remembered. Ilia had came first, one of many from Oscar's tongue that night. Every orgasm caused her skill to falter more and more, until she was only able to bob her head at a weak pace as she felt her body go numb from his mouth. All while he didn't cum once, maybe he was all ready to go at it with his girlfriend at this point. But she couldn't surrender her brother's skill just yet.

When Oscar felt that he wasn't getting as much as he was giving, he was rather peeved. Not that his sister had it coming but he was going to get blue balled. He pulled back from her pussy and tried asking her what happened, only to be met with a pathetic groan. Realizing he was getting nowhere, Oscar rolled his eyes and moved her hips from straddling his face the way they were. Maneuvering her body so she was between his legs and looking at him while his dick was in her mouth. She looked at him in confusion, before feeling his hands firmly yet carefully grab two sides of her head and thrusting his hips.

Oscar began facefucking his sister, his hips bucking up and shoving whatever length of his dick he wanted to be in her mouth. Which was mainly all of it, or at least that's what Ilia thought as she felt her throat get invaded and abused by his cock relentlessly pounding her mouth with such reckless abandon she never thought could come from him. And speaking of coming from him, she heard him groan and grunt as his thrusts grew more sporadic, losing rhythm and pace as his orgasm approached. Placing a hand on the back of her head and pressing her down hard enough to take every single inch of his cock, he came with a drawn out moan. Oscar's load filled his sister's mouth, most of it firing straight down her throat and giving her no choice but to swallow it, which she did rather happily.

As soon as his cock was done shooting his jizz and Ilia drank down pretty much all of it, they both collapsed and just melted into the sheets. Panting and enjoying the feeling of each other's warmth from their bodies, Oscar's hand still interlocked into Ilia's hair and slowly stroking it to relax her. Quite the gentle contrast to his brutal facefuck. As soon as Ilia felt most of her body come back to life, she had crawled up his body and was pulled into a cuddle. Her head contently rested on his chest and her mouth so close to his neck he could feel her breathing on it.

"So... Did you like it?" She asked, smiling and softly giggling at the question. Oscar laughed back, holding her tightly before kissing her forehead.

"There's no way to even describe what I felt, I loved it Ilia." He said.

"Good, then you'll like what we're going to do next time." She mumbled, feeling her mind drift.

"Next time is going to be better? How?" He asked, new interest getting peaked as his eyes widened in curiosity. Ilia heard the question but could not for the life of her find the strength to answer him, as she slowly dozed off to sleep, her brother's embrace too entrancing to fight off sleep. When Oscar heard no answer, he looked down to see his sister's adorable face sleeping so peacefully. He smiled, guessing his question would be answered later. For now, he pulled his blanket over him and his sister, holding her close and joining her in sleep.

* * *

Ilia knew she had nothing to look forward to today, if she didn't have the clear schedule she would've just gone to her room last night. Despite all this, she woke up with no Oscar in sight. She figured he must've had work today. She saw no cars in the driveway except for her own, wondering what'd she do now that she had the chance. She debated setting things up with what's already here at home, or just buy.

_'Eh why not? He deserves it.' _She wondered, shrugging her shoulders before getting out of bed and preparing to look for the right stuff later that night. She had gone shopping at some typical places at the mall, while going the extra mile to a sex shop and get anything that would make it fun, but not complicated for such a young mind Oscar had. She had gotten everything needed for one night, and hoped she'd be able to use all of it. She set everything up in her room, making sure to wash herself just a while before he got back, she knew he must've been waiting for this to happen as much as she was. Her soaked panties were proof of it.

When night came and Oscar was back from work, he went by his normal routine before coming to Ilia's room. He didn't even knock he was anticipating this moment so much. Once he walked in he took in the sight of her room, so set up and clean. No lights were on, as there were many different candles surrounding them and giving Ilia an attractive radiance. After being in her room for a few seconds, he took in the scent of the candles. Most likely vanilla, he remembered hearing the smell was an aphrodisiac. Not that he would need it with the sight of Ilia looking at him with lustful interest.

"I like the decor..." He muttered, unsure of what was happening here. Despite what they've been doing so far and how good it felt, everything about this brought about some anxiety just like when they started.

"I had to make it special, tonight is your final lesson baby brother~" She said, getting out of bed and slowly approaching him. She had a silk robe that covered her shoulders down to her feet, making him wonder what she was hiding.

"Can I see?" He asked as a blush cascaded his face. He may have been nervous but he still wanted this.

"Sure, but you'll have to unwrap your gift before you play with it~" She teased, leaning closer to him and placing a hand on his chest. She could feel his heart pounding already. Without a word, he grabbed the collar of the robe with both hands, she held back her arms and helped him slide it down her body and onto the floor. What Oscar saw absolutely stunned him, his older sister was clad in a black micro bra, long socks stopping above her knees, the same t-back thong, and a garter belt.

"F-fuck..." Was all he could say as he absorbed the sight before him, not sure what else to say. Ilia only giggled in response, before pecking his nose and quickly dropping to her knees. She pulled down his boxers, his hard cock springing free and twitching with need. She moved close to give the tip a kiss before standing back up, grabbing his hand and leading them both to the bed. She had him sit in the same place when she first blew him, back against the wall and her between his spread legs. Just like the night before, she immediately swallowed his cock whole straight down her throat. Though this time she was more slow and passionate, taking her time as if she was teaching a girl to go down on a guy, ironic as the opposite was how this all started.

As soon as Oscar was well lubed and probably might cum within the few minutes, she pulled back and moved up to place her hips right above his. Ilia then reached down to grab his cock, aiming it upwards and using her other hand to slide the fabric of her thong to the side.

"W-wait, what is this now?" He asked, his anxiety at max level as he saw how close his cock was to her pussy. Ilia didn't say anything as she descended, lowering herself and breathing out a hearty moan she didn't even expect. It wasn't until she was at the base of his pelvis did Ilia speak, through hitched breath of course. Her hips slowly rocked against his before leaning in and taking a kiss from him.

"This is the point of all your training, the real deal. You're going to fuck me Oscar." She said, not waiting for a response as she began bouncing already. Ilia didn't realize how much she needed some dick until she finally had one, and she was going to savior it. Oscar placed his hands on her hips to keep her stable as she bounced on his shaft, both of them feeling the rhythm of their love making, up and down, in and out.

The two siblings remained silent as she rode him slow and steady, it was more about the act than the climax this time, as they've already had many climaxes before. Even then, Oscar couldn't even begin to describe the immense pleasure of her warm and wet walls, so velvety while also tight, much better than her mouth. Speaking of, they had began kissing roughly as she rode him, her hands held his face to keep it strong and passionate. They went on kissing and fucking for at least another 10 minutes before Oscar was getting close, the one thing he probably should've brought up before they started. But Ilia made her brother cum enough to tell when he was going to finish.

"Cum in me, I'm safe. Fucking fill me~" She whispered into his ear after separating from their kiss, feeling his dick throb inside her.

"Of fuck! Fuck fuck-" He began groaning and cursing as what was probably his best orgasm of all time took him, calling out his sister's name as he unloaded his cum directly into her. Filling her up so much some of his seed had leaked out, all while Ilia was mewling and shivering as she felt herself get filled with her brother's cum, never having felt so warm and full before.

Their bodies collapsed together once again, though Ilia's chest was right in front of his face, so it was no surprise to feel him gently pepper her torso and breasts with kisses. Their legs intertwined as they held onto each other, feeling something just as great, if not greater than sex while they only cuddled. Once they were done panting and kissing, Ilia stroked his cheek and spoke.

"Well, I can say you're definitely ready for Nora now." Oscar just chuckled and gave a sheepish smile.

"I guess I-I am." He said, his voice a bit sheepish and hesitant, but he just grabbed his things and left as Ilia settled into her bed. Both of them found sleep much easier after that.


	3. Bonus

**Just a mini chapter, an epilogue in a way because I wanted an excuse to throw in another sex scene with these two.**

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Oscar wasn't sure what he was thinking when he approached Ilia's door, he only felt the need to be there after his day. His date was going to start in about half an hour but... It was more than routine, it felt right in a way. Shaking his head and realizing the more time wasted would just end up with Ilia going to sleep and his chance gone. He walked in with no knock, probably not the most welcome thing to do but he figured it was pointless now.

Ilia all but confirmed this when she saw him and smiled as soon as her little brother walked in. But as soon as it appeared, her smile faltered as she saw how gloomy and anxious her brother looked. She sat by the edge of her bed and motioned him to sit right beside her.

"Something on your mind?" She asked, casually leaning in to kiss his cheek and run a hand through his hair. They hadn't given this type of affection to each other since they were little, though it wasn't as weird as it may have been considering their recent activities. Still, the fact she did that despite no planned sexual involvement was going to happen made him shiver and blush.

"J-just a bit nervous about tonight... Y'know?" He said, looking down and clearly thinking hard.

"Oh, right. I thought you'd be more confident now, we learned a lot." She said, hoping to raise his spirits as her smiled returned. He didn't have to look to know, he felt a weak smile come and go.

"I know, it's just... We've really experienced a lot together, Ilia. You made me feel pleasure I've never even imagined was real, and I can't just take that practice onto someone else so quickly. I just... I just wanna keep this up with you." He confessed. Ilia felt touched, unable to speak for a few seconds.

"Oh Oscar... That's so sweet of you. Really heartwarming. But I've never been truly exclusive to a guy before, and you still have a long line of potential just waiting for you. I'm not sure how things might go with you and Nora, but you have an open path full of new and more experiences, you'll just miss out with them if you're hanging onto your big sister." It hurt to say, which was surprising to her. As tempting as it was, Ilia knew she'd only be limited her brother's sex life if they just had each other.

Oscar just nodded, giving a small hum once he understood. The two remained in silence, the only noise being Ilia's dainty fingers going through Oscar's hair. Until he spoke again.

"How about updates? Maybe once a month or every two weeks? Think of it as testing my skills." Ilia just laughed, shaking her head before pecking his cheek.

"Maybe... Only if you mean it as an update thing and not a 'taking advantage of my smoking hot sister to keep fucking her' thing." They both laughed and were relived to ease that tension, giving Oscar hope. Once that was settled, Oscar exited her room and got ready for his date. Since it was a home date, they didn't have to worry too much on clothes or spending money. Nora made them a frozen pizza, (Though it was Oscar's idea, as she begged him to have pancakes for dinner for a rough 15 minutes before caving in) and then they watched a movie. Once it was over, there was only one thing on their minds.

It was as if the movie ending and TV shutting off lit a new mood in the room, as Oscar felt his nerves rise the instant she turned to him and gave a knowing look. He only looked back at her and nodded, before she stood up and lead him by the hand to her room upstairs. Needless to say, Nora was more than surprised by his abilities to blow her mind the way he did. She thought he must've been taking lessons but knew it was too silly of an idea.

Once their copulating was over, Nora told him they'd do the same thing next week and maybe even more. He had no idea was more there was to do, but smiled like an idiot anytime he thought about it. Once he made it back home however, he had passed Ilia's room and noticed the light was on from under her door frame. He figured she would've wanted answers and all the juicy details, so he made way to her room and walked right in.

But once he did, all he saw the was the sight of his older sister napping with her lamp dimly lighting the room as well as her body. Maybe it was the lighting, but Oscar was already getting hard upon seeing her nude form almost glowing with the way the light hit her, especially with the fact she was sleeping on her belly, thus giving him full view to her perfectly round ass. Fueled by temptation and the pretense that this would be fine, Oscar's hands began grabbing and kneading her ass. He felt it before but not quite to his heart's content. He wanted to simply cop a lucky feel, but soon he grew bold and reckless as he squeezed and played with her ass.

He heard a sharp breath leave her and froze, hoping he wasn't caught. But he knew he woke her up, as Ilia's upper half turned to face him, eyes barely opened and yawning oh so cutely.

"Keep going..." She mumbled, clearly tired but not saying no. He was taken back but didn't think twice as he heard this, decided to one up the touching as he opened her legs more and buried his face right into her pussy. He proceeded to eat out his sister and bring many moans from her, waking her up and bringing life to her body as she reached to press his head closer. He noticed her desire for more and introduced his middle finger inside her, pumping it in and out while his tongue rapidly licked her folds.

"O-oscar... Mmm~" She moaned, her other hand grabbing a breast and squeezing. Having just woke up made her feel sensitive, sensing an orgasm approaching already. Her hips grinded against his face and her gasps grew sharper, telling him she close. Wasting no time, Oscar brought his mouth to her clit and sucked the best he could, which was more than enough as Ilia felt herself practically explode with euphoria. Crying out his name weakly before falling flat on her back and panting. She looked up to see her younger brother on his knees, a tent in his pants and a questioning look of need in his eyes. She only nodded, it was all he needed.

Oscar quickly brought himself down Over Ilia, planting a deep kiss on her mouth while his hands grabbed her breasts. Her hands in turn began undoing his pants, pulling them down and immediately grabbing his cock, stroking it to full length. They both moaned into the kiss before pulling away, eyes piercing into one another, conveying only love mixed with primal lust. Ilia helped guide her brother's cock straight to her entrance, once he felt it he thrusted himself right in. He knew not to be so gentle, having fucked her the previous night as well as his girlfriend only hours ago.

Ilia's legs quickly separated for him and then wrapped around his waist, helping him stay and remain until they were done. Oscar couldn't argue, in fact he rather liked it. But what he liked more was the feeling of Ilia's warm and wet walls surrounding his cock as he thrusted away, holding her close in his arms as she cried and mewled out moans like sweet music. Despite what he just did with Nora, there was something about being inside his sister and fucking her good that just felt right. Not exactly better in quality but what was better for him. He felt more and more pulled in by the feeling of his sister and the way she reacted to him, how passionate she was during their love making.

That, as well as literally feeling pulled by her tight pussy naturally trying to bring his cock back in every time he pulled back, only to feel himself sheathed right back in. There was nothing fast or needed as they fucked, just Oscar's mouth kissing her cheek and neck, as well as Ilia's surprising strength as her arms wrapped around his neck and held him close, begging him to never stop. And that was a promise he would hold even if it killed him.

Slow and steady, silent as their bodies intertwined in their heated passion. More about the journey than the destination as Oscar only cared to make his loving sister feel as amazing as she did for him (Not to say that his own pleasure wasn't as satisfying). No words were exchanged as Oscar finally came after who knows how long, groaning Ilia's name through gritted teeth as he came, while she dramatically moaned out his as she came upon feeling the sudden warmth of his hot seed filling her womb. They basked in the afterglow of their sex as Oscar turned over to lie on his back. They breathed heavily and just relaxed.

He wasn't too sure on what to do, as their lovemaking session was rather improvised and not planned with any intended goal... Did it need one? The pleasure was amazing yes, but it basically went against what Ilia told him about only relying on each other to pursue more carnal desire. He didn't even know if he should've left, he felt like getting up until Ilia turned over and lazily draped and arm around his chest, snuggling herself close to him. He smiled and used an arm to bring her in close, her head resting on his chest and their legs interlocking. Oscar wasn't sure what she wanted from this, and saw the only easy thing to do was lean in and place a small kiss on her nose. She giggled.

"You know, I guess weekly updates wouldn't be so bad." She whispered before kissing his chest and nuzzling into him.

"Yeah... Or maybe every couple days." He said, half joking and half hopeful. Ilia just playfully punched him before reaching for her blanket and covering them both.

"Hold onto the energy for later, the anticipation makes it better." And with that, as well as a cute yawn, she drifted asleep in her bother's embrace. Oscar slowly followed after.


End file.
